19-Hydroxy-PG amides

ABSTRACT

The present invention provides novel 19-hydroxy-PG amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a division of Ser. No. 025,899, filed Apr. 2, 1979, now U.S. Pat. No. 4,228,104.

BACKGROUND OF THE INVENTION

The present invention relates to novel prostaglandin analogs. Particularly, these compounds are analogs of the prostaglandins wherein the C-19 position is substituted by hydroxy, i.e., 19-hydroxy-PG compounds. Most particularly, the present invention relates to novel 19-hydroxy-PG amides, a disclosure of the preparation and use of which is incorporated here by reference from U. S. Pat. No. 4,228,104.

Prior Art

Prostaglandin analogs exhibiting hydroxylation in the 19-position are known in the art. See, for example, U.S. Pat. No. 4,127,612, SiH, J.C., Prostaglandins 13:831 (1977 ) and U.S. Pat. Nos. 3,657,316, 3,878,046, and 3,922,297. See also the additional references cited in U.S. Ser. No. 025,899.

SUMMARY OF THE INVENTION

The present invention particularly provides:

A compound of the formula ##STR1## wherein D is

(1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,

(2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --,

(3) cis--CH₂ --CH═CH--CH₂ --CH₂ --,

(4) trans--(CH₂)₃ --CH═CH--,

(5) --(CH₂)₃ --(CH₂)_(g) --CH₂ --,

(6) --(CH₂)₃ --CH₂ --CF₂ --,

(7) --(CH₂)₃ --O--CH₂ --,

(8) --(CH₂)₂ --O--(CH₂)₂ --,

(9) --CH₂ --O--(CH₂)₃ --,

(10) (m--ph) (CH₂)₂ --, or

(11) (m--ph)--O--CH₂ --

wherein m--Ph is inter-meta-phenylene, and wherein g is zero, one, two, or three; wherein Q is α--OH:β--R₅ or α--R₅ :β--OH,

wherein R₅ is hydrogen or methyl, wherein one of R₇ and R₈ is hydrogen and the other is --SO₂ R₂₉ or

wherein R₇ and R₈ are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; wherein R₂₉ is hydrogen, alkyl of one to 12 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl groups of one to 3 carbon atoms, inclusive, or phenyl substituted with hydroxycarbonyl or alkoxycarbonyl of one to 4 carbon atoms, inclusive;

wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl; wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein W is oxo, methylene, α--OH:β--H, or α--H:β--OH; and wherein X is cis- or trans--CH═CH--, --C.tbd.C--, or --CH₂ CH₂ --.

With regard to the divalent the substituents described above (e.g., Q) these divalent radicals are defined as α--R_(I) :β--R_(J), wherein R_(I) represents the substituent of the divalent moiety in the alpha configuration with respect to the ring and R_(j) represents the substituent of the divalent moiety in the beta configuration with respect to the plane of the ring. Accordingly, when Q is defined as α--OH:β--R₅, the hydroxy of the Q moiety is in the alpha configuration, i.e., as in the natural prostaglandin, and the R₅ substituent is in the beta configuration.

Specific embodiments of the present invention include:

19(R)-19-hydroxy-PGF₂α, amide,

11-deoxy-19(R)-19-hydroxy-PGF₂α, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₂α, amide,

19(R)-19-hydroxy-PGF₂β, amide,

11-deoxy-19(R)-hydroxy-PGF₂β, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₂β, amide,

19(R)-19-hydroxy-PGE₂, amide,

11-deoxy-19(R)-19-hydroxy-PGE₂, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₂. amide,

9-deoxo-9-methylene-19(R)-19-hydroxy-PGE₂, amide,

9-deoxo-9-methylene-11-deoxy-19(R)-19-hydroxy-PGE₂, amide,

9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGE.sub.2, amide,

4,5-didehydro-19(R)-19-hydroxy-PGF₁α, amide,

4,5-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁α, amide,

4,5,13,14 -tetradehydro-19(R)-19-hydroxy-PGF₁α, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁α, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁α, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁.alpha., amide,

4,5-dideoxy-19(R)-19-hydroxy-11-deoxy-11α-hydroxy- methyl-PGF₁α, amide,

4,5-dideoxy-19(R)-19-hyroxy-11-deoxy-11α-hydroxy-methyl-15(S)-15-methyl-PGF₁α, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11αhydroxymethyl-PGF₁α, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁α, amide,

4,5-didehydro-19(R)-19-hydroxy-PGF₁β, amide,

4,5-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁β, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁.beta., amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxy-methyl-PGF₁.beta., amide,

4,5-didehydro-19(R)19-hydroxy-11-deoxy-11α-hydroxy-methyl-15(S)-15-methyl-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁β, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α,

hydroxymethyl-16,16-difluoro-PGF₁β, amide,

4,5-didehydro-19(R)-19-hydroxy-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hyroxy-16,16-difluoro-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGE₁, amide,

4,5,13,14-tetrahydro-19(R)-19-hydroxy-11-deoxy-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE.sub.1, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-19-deoxo-9-methylene-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-16,16-difluoro-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE.sub.1, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-PGE.sub.1, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-16,16difluoro-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, amide,

4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11.alpha.-hydroxy-methyl-PGE₁, amide,

4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11.alpha.-hydroxmethyl-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19- hydroxy-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁.alpha., amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁α, amide,

2,3-didehydro-19(R)-19-hydroxy-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-15(S)-methyl-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, amide

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁.beta., amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁β, amide,

2,3-didehydro-19(R)-19-hydroxy-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE.sub.1, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁, amide,

2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-15(S)-15-methyl-PGE₁, amide,

19(R)-19-hydroxyPGF₁α, amide,

16,16-dimethyl-19(R)-19-hydroxy-PGF₁α, amide,

16,16-difluoro-19(R)-19-hydroxy-PGF₁α, amide,

13,14-dihydro-19(R)-19-hydroxy-PGF₁α, amide,

11-deoxy-19(R)-19-hyroxy-PGF₁α, amide,

11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGF₁α, amide,

11-deoxy-16,16-difluoro-19(R)-19-hydroxy-PGF₁α, amide,

11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGF₁α, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₁α, amide,

11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGF₁.alpha., amide,

11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGF₁.alpha., amide,

11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hyroxy-PGF₁.alpha., amide,

19(R)-19-hydroxy-PGF₁β, amide,

16,16-dimethyl-19(R)-19-hydroxy-PGF₁β, amide,

16,16-difluoro-19(R)-19-hydroxy-PGF₁β, amide,

13,14-dihydro-19(R)-19-hydroxy-PGF₂β, amide,

11-deoxy-19(R)-19-hydroxy-PGF₁β, amide,

11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGF₁β, amide,

16,16-difluoro-19(R)-19-hydroxy-PGF₁β, amide,

11-deoxy-13,14-dihydro-19-(R)-19-hydroxy-PGF₁β, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₁β, amide,

11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGF₁.beta., amide,

11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGF₁.beta., amide,

11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGF₁.beta., amide,

19(R)-19-hydroxy-PGE₁, amide,

16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

11deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19(R)- 19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide,

9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide,

The compounds of the present invention are particularly useful for including prostaglandin-like biological effects, as is described in Ser. No. 025,899. Uses of compounds in accordance with the present invention include, therefore, anti-asthmatic indications. 

I claim:
 1. A compound of the formula ##STR2## wherein D is (1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --,(2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --, (3) cis--CH₂ --CH═CH--CH₂ --CH₂ --, (4) trans--(CH₂)₃ --CH═CH--, (5) --(CH₂)₃ --(CH₂)_(g) --CH₂ --, (6) --(CH₂)₃ --CH₂ --CF₂ --, (7) --(CH₂)₃ --O--CH₂ --, (8) --(CH₂)₂ --O--(CH₂)₂ --, (9) --CH₂ --O--(CH₂)₃ --, (10) --(m--ph)--(CH₂)₂ --, or (11) --(m--ph)--O--CH₂ --wherein m--ph is inter-meta-phenylene, and wherein g is zero, one, two, or three; wherein Q is α--OH:β--R₅ or α--R₅ :β--OH, wherein R₅ is hydrogen or methyl, wherein one of R₇ and R₈ is hydrogen and the other is --SO₂ R₂₉ or wherein R₇ and R₈ are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different; wherein R₂₉ is hydrogen, alkyl of one to 12 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl groups of one to 3 carbon atoms, inclusive, or phenyl substituted with hydroxycarbonyl or alkoxycarbonyl of one to 4 carbon atoms, inclusive; wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl; wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein W is oxo, methylene, α--OH:β--H, or α--H:β--OH; and wherein X is cis-- or trans--CH═CH--, --C.tbd.C--, or --CH₂ CH₂ --.
 2. A compound according to claim 1, wherein g is one or three.
 3. A compound according to claim 2, wherein D is cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --.
 4. A compound according to claim 3, wherein W is ##STR3##
 5. A compound according to claim 4, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 6. 19(R)-19-hydroxy-PGF₂α, amide, a compound according to claim
 5. 7. A compound according to claim 4, wherein R₂ is hydrogen and X is trans--CH═CH--.
 8. 11-deoxy-19(R)-19-hydroxymethyl-11-deoxy-19(R)-19-hydroxy-PGF 2.sub.α, amide, a compound according to claim
 7. 9. A compound according to claim 4, wherein R₂ is hydroxymethyl and X is trans--CH═CH--.
 10. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₂α, amide, a compound according to claim
 9. 11. A compound according to claim 3, wherein W is ##STR4##
 12. A compound according to claim 11, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 13. 19(R)-19-hydroxy-PGF₂β, amide, a compound according to claim
 12. 14. A compound according to claim 11, wherein R₂ is hydrogen and X is trans--CH═CH--.
 15. 11-deoxy-19(R)-hydroxy-PGF₂β, amide, a compound according to claim
 14. 16. A compound according to claim 11, wherein R₂ is hydroxymethyl and X is trans--CH═CH--.
 17. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₂β, amide, a compound according to claim
 16. 18. A compound according to claim 3, wherein W is ##STR5##
 19. A compound according to claim 18, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 20. 19(R)-19-hydroxy-PGE₂, a compound according to claim
 19. 21. A compound according to claim 19, wherein R₂ is hydrogen and X is trans--CH═CH--.
 22. 11-deoxy-19(R)-19-hydroxy-PGE₂, amide, a compound according to claim
 21. 23. A compound according to claim 18, wherein R₂ is hydroxymethyl and X is trans--CH═CH--.
 24. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGE₂, amide, a compound according to claim
 23. 25. A compound according to claim 3, wherein W is ##STR6##
 26. A compound according to claim 25, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 27. 9-deoxo-9-methylene-19(R)-19-hydroxy-PGE₂, amide, a compound according to claim
 26. 28. A compound according to claim 25, wherein R₂ is hydrogen and X is trans--CH═CH--.
 29. 9-deoxo-9-methylene-11-deoxy-19(R)-19-hydroxy-PGE₂, amide, a compound according to claim
 28. 30. A compound according to claim 25, wherein R₂ is hydroxymethyl and X is trans--CH═CH--.
 31. 9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGE₂, amide, a compound according to claim
 30. 32. A compound according to claim 2, wherein D is cis--CH₂ --CH═CH--CH₂ --CH₂ --.
 33. A compound according to claim 32, wherein W is ##STR7##
 34. A compound according to claim 33, wherein R₂ is hydroxyl.
 35. A compound according to claim 34, wherein X is trans--CH═CH--.
 36. 4,5-didehydro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 35. 37. 4,5-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 35. 38. A compound according to claim 34, wherein X is --C.tbd.C--.
 39. 4,5,13,14,-tetradehydro-19(R)-19-hydroxy-PGF₁α amide, a compound according to claim
 38. 40. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁α, amide, a compound according to claim
 38. 41. A compound according to claim 33, wherein R₂ is hydrogen.
 42. A compound according to claim 41, wherein X is trans--CH═CH--.
 43. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide, a compound according to claim
 42. 44. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 42. 45. A compound according to claim 41, wherein X is --C.tbd.C--.
 46. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide, a compound according to claim
 45. 47. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁α, amide, a compound according to claim
 45. 48. A compound according to claim 33, wherein R₂ is hydroxymethyl.
 49. A compound according to claim 48, wherein X is trans--CH═CH--.
 50. 4,5-dideoxy-19(R)-19-hydroxy-11-deoxy-11α-hydroxy-methyl-PGF₁α, amide, a compound according to claim
 49. 51. 4,5-dideoxy-19(R)-19-hydroxy-11-deoxy-11α-hydroxy-methyl-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 49. 52. A compound according to claim 48, wherein X is --C.tbd.C--.
 53. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁α, amide, a compound according to claim
 52. 54. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁α, amide, a compound according to claim
 52. 55. A compound according to claim 32, wherein W is ##STR8##
 56. A compound according to claim 55, wherein R₂ is hydroxyl.
 57. A compound according to claim 56, wherein X is trans--CH═CH--.
 58. 4,5-didehydro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 57. 59. 4,5-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁β, amide, a compound according to claim
 57. 60. A compound according to claim 56, wherein X is --C.tbd.C--.
 61. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 60. 62. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁β, amide, a compound according to claim
 60. 63. A compound according to claim 55, wherein R₂ is hydrogen.
 64. A compound according to claim 63, wherein X is trans--CH═CH--.
 65. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, a compound according to claim
 64. 66. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁β, amide, a compound according to claim
 64. 67. A compound according to claim 63, wherein X is --C.tbd.C--.
 68. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, amide, a compound according to claim
 67. 69. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁β, amide, a compound according to claim
 67. 70. A compound according to claim 55, wherein R₂ is hydroxymethyl.
 71. A compound according to claim 70, wherein X is trans--CH═CH--.
 72. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxy-methyl-PGF₁β, amide, a compound according to claim
 71. 73. 4,5-didehydro-19(R)-19-hyroxy-11-deoxy-11α-hydroxy-methyl-15(S)-15-methyl-PGF₁β, amide, a compound according to claim
 71. 74. A compound according to claim 70, wherein X is --C.tbd.C--.
 75. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁β, amide, a compound according to claim
 74. 76. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁β, amide, a compound according to claim
 74. 77. A compound according to claim 32, wherein W is ##STR9##
 78. A compound according to claim 77, wherein R₂ is hydroxyl.
 79. A compound according to claim 78, wherein X is trans--CH═CH--.
 80. 4,5-didehydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 79. 81. 4,5-didehydro-19(R)-19-hydroxy-15(S)-15methyl-PGE₁, amide, a compound according to claim
 79. 82. A compound according to claim 78, wherein X is --C.tbd.C--.
 83. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 82. 84. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-16,16-difluoro-PGE₁, amide, a compound according to claim
 82. 85. A compound according to claim 77, wherein R₂ is hydrogen.
 86. A compound according to claim 85, wherein X is trans--CH═CH--.
 87. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-PGE₁, a compound according to claim
 86. 88. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 86. 89. A compound according to claim 85, wherein X is --C C--.
 90. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-PGE₁, amide, a compound according to claim
 89. 91. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGE₁, amide, a compound according to claim
 89. 92. A compound according to claim 77, wherein R₂ is hydroxymethyl.
 93. A compound according to claim 92, wherein X is trans--CH═CH--.
 94. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxy-methyl-PGE₁, amide, a compound according to claim
 93. 95. 4,5-didehydro-19(R)-19-hydroxy-11-deoxy-11.alpha.-hydroxy-methyl-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 93. 96. A compound according to claim 92, wherein X is --C C--.
 97. 4,5,13,14-tetradehydro19(R)-19-hydroxy-11-deoxy-11.alpha.-hydroxymethyl-PGE₁, amide, a compound according to claim
 96. 98. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-di-fluoro-PGE₁, amide, a compound according to claim
 96. 99. A compound according to claim 32, wherein W is ##STR10##
 100. A compound according to claim 99, wherein R₂ is hydroxyl.
 101. A compound according to claim 100, wherein X is trans---CH═CH--.
 102. 4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-PGE₁, amide, a compound according to claim
 101. 103. 4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 101. 104. A compound according to claim 100, wherein X is --C.tbd.C--.
 105. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-PGE₁, amide, a compound according to claim
 104. 106. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-16,16-difluoro-PGE₁, amide, a compound according to claim
 108. 107. A compound according to claim 99, wherein R₂ is hydrogen.
 108. A compound according to claim 107, wherein X is trans--CH═CH--.
 109. 4,5-didehydro-19(R)-19-hydroxy-9-methylene-11-deoxy-PGE₁, a compound according to claim
 108. 110. 4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 108. 111. A compound according to claim 107, wherein X is --C.tbd.C--.
 112. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-PGE₁, amide, a compound according to claim
 111. 113. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁, amide, a compound according to claim
 111. 114. A compound according to claim 99, wherein R₂ is hydroxymethyl.
 115. A compound according to claim 114, wherein X is trans--CH═CH--.
 116. 4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, amide, a compound according to claim
 115. 117. 4,5-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 115. 118. A compound according to claim 114, wherein X is --C.tbd.C--.
 119. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, amide, a compound according to claim
 118. 120. 4,5,13,14-tetradehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, amide, a compound according to claim
 118. 121. A compound according to claim 2, wherein D is trans--(CH₂)₃ --CH═CH--.
 122. A compound according to claim 121, wherein W is ##STR11##
 123. A compound according to claim 122, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 124. 2,3-didehydro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 123. 125. 2,3-didehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁α, amide, a compound according to claim
 123. 126. 2,3-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 123. 127. A compound according to claim 122, wherein R₂ is hydrogen and X is trans--CH═CH--.
 128. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁α, amide, a compound according to claim
 127. 129. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁α, amide, a compound according to claim
 127. 130. 2,3-didehydro-19(R)-19-hydroxy-11deoxy-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 127. 131. A compound according to claim 122, wherein R₂ is hydroxymethyl, and X is trans--CH═CH--.
 132. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁α, amide, a compound according to claim
 131. 133. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁.alpha., amide, a compound according to claim
 131. 134. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁α, amide, a compound according to claim
 131. 135. A compound according to claim 121, wherein W is ##STR12##
 136. A compound according to claim 135, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 137. 2,3-didehydro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 136. 138. 2,3-didehydro-19(R)-19-hydroxy-16,16-difluoro-PGF₁β, amide, a compound according to claim
 136. 139. 2,3-didehydro-19(R)-19-hydroxy-15(S)-methyl-PGF₁β, amide, a compound according to claim
 136. 140. A compound according to claim 135, wherein R₂ is hydrogen and X is trans--CH═CH--.
 141. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGF₁β, a compound according to claim
 140. 142. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGF₁β, amide, a compound according to claim
 140. 143. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGF₁β, amide, a compound according to claim
 140. 144. A compound according to claim 135, wherein R₂ is hydroxymethyl, and X is trans--CH═CH--.
 145. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-PGF₁β, amide, a compound according to claim
 144. 146. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁β, amide, a compound according to claim
 144. 147. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁β, amide, a compound according to claim
 144. 148. A compound according to claim 121, wherein W is ##STR13##
 149. A compound according to claim 148, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 150. 2,3-didehydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 149. 151. 2,3-didehydro-19(R)-19-16,16-difluoro-PGE₁, amide, a compound according to claim
 149. 152. 2,3-didehydro-19(R)-19-hydroxy-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 149. 153. A compound according to claim 148, wherein R₂ is hydrogen and X is trans--CH═CH--.
 154. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-PGE₁, amide, a compound according to claim
 153. 155. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-16,16-difluoro-PGE₁, amide, a compound according to claim
 153. 156. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 153. 157. A compound according to claim 148, wherein R₂ is hydroxymethyl, and X is trans--CH═CH--.
 158. 2,3-didehydro-19(R)-19-hydroxy-11deoxy-11α-hydroxymethyl-PGE₁, amide, a compound according to claim
 157. 159. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, amide, a compound according to claim
 157. 160. 2,3-didehydro-19(R)-19-hydroxy-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 157. 161. A compound according to claim 121, wherein W is ##STR14##
 162. A compound according to claim 161, wherein R₂ is hydroxyl and X is trans--CH═CH--.
 163. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-PGE₁, amide, a compound according to claim
 162. 164. 2,3didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-16,16-difluoro-PGE₁, amide, a compound according to claim
 162. 165. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 162. 166. A compound according to claim 161, wherein R₂ is hydrogen and X is trans--CH═CH--.
 167. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-PGE₁, amide, a compound according to claim
 166. 168. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁, amide, a compound according to claim
 166. 169. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-15(S)-15-methyl-PGE₁, amide, a compound according to claim
 166. 170. A compound according to claim 161, wherein R₂ is hydroxymethyl, and X is trans--CH═CH--.
 171. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, amide, a compound according to claim
 170. 172. 2,3-didehydro-19(R)-19-hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, a compound according to claim
 170. 173. 2,3-didehydro-19(R)-₁₉ -hydroxy-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15-(S)-15-methyl-PGE₁, amide, a compound according to claim
 170. 174. A compound according to claim 2, wherein D is --(CH₂)₃ --(CH₂)_(g) --CH₂ --, wherein g is zero, one, two or three.
 175. A compound according to claim 174, wherein g is one.
 176. A compound according to claim 175, wherein W is ##STR15##
 177. A compound according to claim 176, wherein R₂ is hydroxyl.
 178. A compound according to claim 177, wherein X is trans--CH═CH--.
 179. 19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 178. 180. 16,16-dimethyl-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 178. 181. 16,16-difluoro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 178. 182. A compound according to claim 177, wherein X is --CH₂ CH₂ --.
 183. 13,14-dihydro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 182. 184. A compound according to claim 176, wherein R₂ is hydrogen.
 185. A compound according to claim 184, wherein X is trans--CH═CH--.
 186. 11-deoxy-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 185. 187. 11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 185. 188. 11-Deoxy-16,16-difluoro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 185. 189. A compound according to claim 184, wherein X is --CH₂ CH₂ --.
 190. 11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 189. 191. A compound according to claim 176, where R₂ is hydroxymethyl.
 192. A compound according to claim 191, wherein X is trans--CH═CH--.
 193. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 192. 194. 11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 192. 195. 11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGF₁α, amide, a compound according to claim
 192. 196. A compound according to claim 191, wherein X is --CH₂ CH₂ --.
 197. 11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGF.sub.1α, amide, a compound according to claim
 196. 198. A compound according to claim 175, wherein W is ##STR16##
 199. A compound according to claim 198, wherein R₂ is hydroxyl.
 200. A compound according to claim 199, wherein X is trans--CH═CH--.
 201. 19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 200. 202. 16,16-dimethyl-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 200. 203. 16,16-difluoro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 200. 204. A compound according to claim 199, wherein X is --CH₂ CH₂ --.
 205. 13,14-dihydro-19(R)-19-hydroxy-PGF₂β, amide, a compound according to claim
 204. 206. A compound according to claim 198, wherein R₂ is hydrogen.
 207. A compound according to claim 206, wherein X is trans--CH═CH--.
 208. 11-deoxy-19(R)-19-hydroxy-PGF₁β, a compound according to claim
 207. 209. 11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 207. 210. 16,16-difluoro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 207. 211. A compound according to claim 206, wherein X is --CH₂ CH₂ --.
 212. 11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 211. 213. A compound according to claim 198, wherein R₂ is hydroxymethyl.
 214. A compound according to claim 213, wherein X is trans--CH═CH--.
 215. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 214. 216. 11-deoxy-11α-hydroymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 214. 217. 11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGF₁β, amide, a compound according to claim
 214. 218. A compound according to claim 213, wherein X is --CH₂ CH₂ --.
 219. 11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGF.sub.1β, amide, a compound according to claim
 218. 220. A compound according to claim 175, wherein W is ##STR17##
 221. A compound according to claim 220, wherein R₂ is hydroxyl.
 222. A compound according to claim 221, wherein X is trans--CH═CH--.
 223. 19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 222. 224. 16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 222. 225. 16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 222. 226. A compound according to claim 221, wherein X is --CH₂ CH₂ --.
 227. 13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 226. 228. A compound according to claim 220, wherein R₂ is hydrogen.
 229. A compound according to claim 228, wherein X is trans--CH═CH--.
 230. 11-deoxy-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 229. 231. 11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 229. 232. 11-deoxy-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 229. 233. A compound according to claim 228, wherein X is --CH₂ CH₂ --.
 234. 11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 233. 235. A compound according to claim 220, wherein R₂ is hydroxymethyl.
 236. A compound according to claim 235, wherein X is trans--CH═CH--.
 237. 11-deoxy-11α-hydroxymethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 236. 238. 11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 236. 239. 11-deoxy-11α-hydroxymethyl-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 236. 240. A compound according to claim 235, wherein X is --CH₂ CH₂ --.
 241. 11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGE.sub.1, amide, a compound according to claim
 240. 242. A compound according to claim 175, wherein W is ##STR18##
 243. A compound according to claim 242, wherein R₂ is hydroxyl.
 244. A compound according to claim 243, wherein X is trans--CH═CH--.
 245. 9-deoxo-9-methylene-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 244. 246. 9-deoxo-9-methylene-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 244. 247. 9-deoxo-9-methylene-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 244. 248. A compound according to claim 243, wherein X is --CH₂ CH₂ --.
 249. 9-deoxo-9-methylene-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 248. 250. A compound according to claim 242, wherein R₂ is hydrogen.
 251. A compound according to claim 250, wherein X is trans--CH═CH--.
 252. 9-deoxo-9-methylene-11-deoxy-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 251. 253. 9-deoxo-9-methylene-11-deoxy-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 251. 254. 9-deoxo-9-methylene-11-deoxy-16,16-difluoro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 251. 255. A compound according to claim 250, wherein X is --CH₂ CH₂ --.
 256. 9-deoxo-9-methylene-11-deoxy-13,14-dihydro-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 255. 257. A compound according to claim 242, wherein R₂ is hydroxymethyl.
 258. A compound according to claim 257, wherein X is trans--CH═CH--.
 259. 9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19-(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 258. 260. 9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19(R)-19-hydroxy-PGE₁, amide, a compound according to claim
 258. 261. 9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl- 16,16-difluoro-19(R)-19-hydroxy-PGE₁,amide, a compound according to claim
 258. 262. A compound according to claim 257, wherein X is --CH₂ CH₂ --.
 263. 9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19(R)-19-hydroxy-PGE₁, a compound according to claim
 262. 